2-Fluoro-4-nitroaniline → 3-Benzyl-5-((2-fluoro-4-nitrophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

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Reaction Steps

3-Benzyl-5-chloro-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (950 mg, 3.15 mmol, 1 eq), 2-fluoro-4-nitroaniline (540 mg, 3.46 mmol, 1.1 eq), tris(dibenzylideneacetone)dipalladium(0) (58 mg, 0.06 mmol, 0.02 eq), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (36 mg, 0.06 mmol, 0.02 eq) and sodium tert-butoxide (453 mg, 4.7 mmol, 1.5 eq) were mixed in degassed anhydrous dioxane (7 mL) and subjected to microwave irradiation at 100° C. for 30 minutes. Upon cooling a precipitate formed which was filtered and washed with cold dioxane (3 mL) to give 910 mg of the title compound (69%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.55 (s, 3 H) 5.23 (s, 2 H) 6.14 (s, 1 H) 7.29-7.41 (m, 5 H) 7.81-7.94 (m, 1 H) 8.14 (d, J=10.86 Hz, 1 H) 8.25 (d, J=11.12 Hz, 1 H) 8.96 (s, 1 H) 11.23 (s, 1 H) [M+H] calc'd for C21H16FN5O4, 422; found, 422.

Provenance & Evidence